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Compiled and edited by Julie Tereshchuk

Dear Mentors,

We just interviewed a great candidate, who would be my direct report. The only wrinkle in hiring her is that she really wants to work from home for most of the week. I’d be willing, but how do I persuade my unenthusiastic boss?



Mid March Editorial Update:  We know “work from home” just got much more wide spread. Lani Rosales updated her response with some COVID-19 specific advice. Stay tuned as we address some of the new challenges you may be facing in upcoming columns.

Dear Mentee,

What I’ve learned being fully remote for the last year and peeking (as a consultant) inside hundreds of companies over the last 12 years: much of the resistance to having knowledge workers do their job from home can be attributed to one of two things: no clear work plan tied to success metrics, or a culture of lazy internal communication.

In the first scenario, employees don’t know when they walk in the door what they should be doing for the day/week/quarter or how they would know if they were succeeding. The job is to be responsive to the needs of the company and customers as they arise, and therefore being in the same space as the rest of the team is critical to everyone figuring out what they’re supposed to be working on next.

In the second case, communication has become lazy, last-minute, and reliant on meetings and face-time to share important info. The founder of Basecamp (fully remote from day one) has written a brilliant guide to internal communication that I find really useful for helping teams get a baseline of how “fit” or “lazy” their communication style is:

To address these two issues, define the role by how much they accomplish rather than how long they stare at the screen, and set a clear expectation of proactive, written communications and usually the work speaks for itself.


Jenny Magic


Dear Mentee,

Your boss needs an attitude adjustment! Productivity is not a matter of where an employee works, but how. Someone who struggles with distractions, procrastination, or who gets lost in busy work at a cost of real productivity, will have those issues regardless of their work location.

Ensure that all employees have modern skills to manage their busy workloads, and evaluate performance based on outcomes rather than face-time in the office.


Maura Thomas


Dear Mentee,

The good news is that if YOU have already bought into this candidate working from home, your boss is more likely to. But you mentioned a lack of enthusiasm, so let’s think about it from a business perspective. Let’s make it a win for them! Ask your boss if you can meet with them about a fantastic candidate, and while you wait for their response, scramble to do your research!

Prepare a simple proposal focused on how this candidate working remotely for most of the week benefits the company. Make it about them. Assuage their fears (which will be primarily productivity and availability).

Consider a trial period wherein the candidate works from home for 3 days a week for the first 30 days, then 4 if that works effectively for all stakeholders. Avoid a scheduling proposal that could be translated as someone who really just wants a long weekend. Shoot for more days than you think your boss will offer so you have some negotiating room, which will allow them to feel like they won. If a 3-out, 2-in week is the goal, shoot for 4-out, 1-in at first and let them tell you a 3-2 is better.

Put thought into communication requirements that would make this work. If it is a salaried position, you’ll have more flexibility, but either way, what response times are expected via phone when she is remote? Email response times? Slack?

Are you prepared to act in a mentor capacity with a remote worker to help them to navigate the ropes, and take responsibility for their adapting to the work culture despite being in another location? Proposing this candidate will inadvertently put you in this role, so if you’re willing, go ahead and include this as part of your pitch with your boss, and include some basic logistics (“I intend on meeting with this candidate every Tuesday from 1-2pm via video to act as a liaison for the company to make sure they are meeting our expectations, and guide them into success with the role in a mentor capacity.”)

Can you train this person to over-communicate so your boss is always looped in? And, how will you deal with it if they fall short and don’t update the project management platform, for example.

Consider any savings for the company this might provide. Aside from real estate (more on-site employees equals more space necessary), equipment costs are typically lower as remote workers are often expected to use their own, utility costs are lower with one less person in the office, perks like snacks and drinks cost less when a remote worker is off-site, and so forth.

Lastly, consider using a different word if your boss is ultra traditional. “Remote” work may sound too trendy. “Telecommute” might pique their interest instead!

For some stats to beef up your proposal, check this info out:

  1. Global telecommuting trends (ex: Businesses save an average of $11,000 per half-time telecommuter per year)
  2. Remote workers take less sick days and are generally healthier (talk about savings!)
  3. World Economic Forum acknowledged the growing trend (ex: Flexible work is “one of the biggest drivers of transformation of business models in many industries.”)
  4. Loyalty is higher for remote workers, and many would take a flexible work option over a raise if given the choice
  5. America’s biggest and most successful companies offer remote roles (like Dell, Amazon, Cisco, Hilton, SAP, vmware, Intuit, Aetna and many more)
  6. Remote workers are more productive
  7. Offering select remote roles can attract higher quality talent, retain them, and is a non-monetary incentive
  8. Remote workers stick around longer (and cost the company less in turnover costs)
  9. 25 more important remote work stats for 2020

And if they say no, at least now you’re basically an expert on remote work. 😉


Lani Rosales


Lani’s COVID-19 Update:

When the dust settles in a post-COVID-19 world, it is going to be a challenge getting all workers back into the office. Many will be nervous, and others are already looking for a new job that is always remote. Let’s be honest, most people didn’t know that remote work might be their jam. 

If you’re one of those people that have found yourself to be more productive during this time, and enjoyed a better work-life balance now that traffic and primping aren’t part of your day, you might be pondering how to pitch to your boss that you’d like to remain at home. 

Some companies will be amenable, others will not, and there’s no way to tell quite yet where each will land. But if you’ve done your research, it is worth pitching when they start calling teams back in. And not just for yourself. Referencing some of the aforementioned data linked to, you can make a case for remote work being a tool the company uses for recruiting in this new world. 

Many people won’t cut it as remote workers, and others will thrive – team decks will be shuffled. Empowering your boss with the information needed to understand that remote work possibilities are another cost saving measure and recruiting tool can improve the company’s long-term bottom line. And also you don’t want to wear shoes anymore, amirite!?